EP3135679A1 - Neuartige bis-(alkoxysilyl-vinylen)-gruppenhaltige siliciumverbindung und herstellungsverfahren dafür - Google Patents

Neuartige bis-(alkoxysilyl-vinylen)-gruppenhaltige siliciumverbindung und herstellungsverfahren dafür Download PDF

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Publication number
EP3135679A1
EP3135679A1 EP15782603.3A EP15782603A EP3135679A1 EP 3135679 A1 EP3135679 A1 EP 3135679A1 EP 15782603 A EP15782603 A EP 15782603A EP 3135679 A1 EP3135679 A1 EP 3135679A1
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Prior art keywords
group
carbon atoms
vinylene
silicon compound
alkoxysilyl
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EP15782603.3A
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English (en)
French (fr)
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EP3135679B1 (de
EP3135679A4 (de
Inventor
Takahiro Yamaguchi
Takafumi Sakamoto
Taiki KATAYAMA
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Shin Etsu Chemical Co Ltd
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Shin Etsu Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/222—Amides of phosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a novel organic silicon compound, especially a novel organic silicon compound useful as a curing agent with an effect of imparting a superior fast curability to a room temperature-curable organopolysiloxane composition; and a production method thereof.
  • a hydrolyzable silyl group such as an alkoxysilyl group
  • a structure where two silicon atoms are bonded to each other through a carbon-carbon double bond i.e. silyl-vinylene structure or silyl-ethenylene structure.
  • Typical examples of the above type of room temperature-curable composition include a composition composed of a hydroxyl group-terminated polyorganosiloxane, alkoxysilane and an organic titanium compound; a composition composed of an alkoxysilyl group-terminated polyorganosiloxane, alkoxysilane and alkoxy titanium; a composition composed of a linear polyorganosiloxane containing a silethylene group(s) and terminated by alkoxysilyl groups, alkoxysilane and alkoxy titanium; and a composition composed of a hydroxyl group-terminated polyorganosiloxane or an alkoxy group-terminated polyorganosiloxane and an alkoxy- ⁇ -silylester compound (Patent documents 1 to 4).
  • compositions exhibit a storage stability, a water resistance and a moisture resistance to a certain degree, these properties are not yet completely satisfactory. Further, these compositions have so far exhibited an insufficient fast curability.
  • polymers having reactive alkoxysilyl groups on their terminal ends are known. Since these polymers have their polymer terminal ends blocked by alkoxysilyl groups from the beginning, the curability of a composition containing the same is less likely to change (deteriorate) with time, and a superior storage stability can thus be achieved. Further, a workability (viscosity, thixotropy) of such composition can be arbitrarily controlled, and superior properties (hardness, tensile strength and elongation at break) can also be achieved as those polymers form elastomers through reactions with the moisture in the air and then through cross-liking reactions.
  • the present invention was made in view of the above issues, and it is an object of the present invention to provide a curing agent for a room temperature-curable organopolysiloxane composition.
  • the curing agent is especially capable of imparting a fast curability to the room temperature-curable organopolysiloxane composition, and can thus provide a cured product superior in storage stability and durability.
  • the room temperature-curable organopolysiloxane composition can be industrially advantageously produced using a highly general material(s).
  • the inventors of the present invention diligently conducted a series of studies and completed the invention as follows. That is, the inventors found that the hydrolyzability of an alkoxy group in an alkoxysilyl group could be dramatically improved, only when a linking group adjacent to such alkoxysilyl group was a vinylene group (ethenylene group). Specifically, the inventors found that by using a compound that is represented by the following formula (1) and contains alkoxysilyl-vinylene groups, there could be obtained a room temperature-curable composition especially superior in fast curability and capable of forming a cured product with a favorable storage stability and durability.
  • the inventors were able to arrive at a room temperature-curable organopolysiloxane composition that can be industrially advantageously produced due to the fact that a highly general material(s) (e.g. diorgano dichlorosilane) can be used as a part of a starting material(s) for producing the above alkoxysilyl-vinylene group-containing compound.
  • a highly general material(s) e.g. diorgano dichlorosilane
  • the novel silicon-containing compound of the present invention provides a cured product superior in fast curability, and allows a composition using the same to be quickly cured when exposed to the air even after the composition had been stored for 12 months.
  • a cured product thus obtained exhibits superior properties. Therefore, a composition having, as a curing agent, the novel silicon-containing compound of the present invention (e.g. room temperature-curable organopolysiloxane composition) is useful as a sealing agent, coating material or adhesive agent for use in certain locations where heat resistance, water resistance and moisture resistance are required.
  • such composition can be effectively used for construction purposes and applied to an adhesive agent for electric and electronic parts, where steam resistance and water resistance are required.
  • the silicon-containing compound of the present invention uses a general-purpose chlorosilane, it can be easily industrialized.
  • the silicon-containing compound terminated by alkoxysilyl-vinylene group which is represented by the above general formula (1) is that having not less than two alkoxysilyl-vinylene bonds on an identical silicon atom (i.e. bis (alkoxysilyl-vinylene) silane compound).
  • examples of R 1 as an alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group and an eicosyl group.
  • Examples of a cycloalkyl group include a cyclopentyl group and a cyclohexyl group.
  • Examples of an alkyl group that has 1 to 20 carbon atoms and may have a substituted group(s), include an aralkyl group such as a benzyl group, a 2-phenylethyl group and a 3-phenylpropyl group.
  • all or a part of the hydrogen atoms in any of these (substituted) alkyl groups may be substituted by, for example, cyano groups and/or halogen atoms such as F, Cl and Br.
  • Examples of a substituted group thus obtained include a 3-chloropropyl group, a 3,3,3-trifluoropropyl group and a 2-cyanoethyl group.
  • preferred as R 1 are alkyl groups having 1 to 6, particularly 1 to 4 carbon atoms.
  • a methyl group and an ethyl group are more preferred as R 1 , where a methyl group is even more preferred in terms of availability, productivity and cost.
  • R 2 represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
  • R 2 s may be identical to or different from one another.
  • Examples of such R 2 include an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an o
  • R 2 may also be a group obtained by substituting a part of or all the hydrogen atoms in any of these groups with, for example, cyano groups and/or halogen atoms such as F, Cl and Br.
  • substituted group include a 3-chloropropyl group, 3,3,3-trifluoropropyl group and a 2-cyanoethyl group.
  • monovalent hydrocarbon groups having 1 to 10, particularly 1 to 6 carbon atoms.
  • a methyl group, an ethyl group and a phenyl group are more preferred, where a methyl group and a phenyl group are even more preferred in terms of availability, productivity and cost.
  • Each a independently represents an integer of 1 to 3. However, it is preferred that a be either 2 or 3, more preferably 3.
  • the organic silicon compound represented by the general formula (1) of the present invention is mainly used as a curing agent for a (room temperature) curable composition.
  • a (room temperature) curable composition Particularly, those having three methoxy groups on an identical silicon atom in a molecule (six in total per molecule) contain a trifunctional alkoxysilane site(s), and are thus useful as curing agents (cross-linking agent) for a dealcoholized silicone RTV (room temperature-curable organopolysiloxane composition).
  • the silicon-containing compound of the invention which has two alkoxysilyl-vinylene bonds on an identical silicon atom can, for example, be easily produced through an addition reaction such as a hydrosilylation reaction between a silane having two ethynyl groups on an identical silicon atom and two alkoxysilanes (hydrogenalkoxysilane).
  • This reaction is expressed by the following formula [1]. (In the above formula, R 1 , R 2 and a are defined as above.)
  • platinum group metal-based catalysts such as a platinum-based catalyst, a palladium-based catalyst, a rhodium-based catalyst and a ruthenium-based catalyst are available.
  • a platinum-based catalyst is particularly preferred.
  • platinum-based catalyst include a platinum black; a catalyst with a solid platinum being supported on a support such as alumina and silica; a chloroplatinic acid; an alcohol-modified chloroplatinic acid; a complex of a chloroplatinic acid and olefin; and a complex of platinum and vinylsiloxane.
  • platinum may be used in a so-called catalytic amount, and may, for example, be used in an amount of 0.1 to 1,000 ppm, particularly 0.5 to 100 ppm in terms of platinum group metal, with respect to alkoxysilanes.
  • this reaction be performed at a temperature of 50 to 120°C, particularly 60 to 100°C, for 0.5 to 12 hours, particularly 1 to 6 hours, and the reaction can be performed without a solvent.
  • an appropriate solvent such as toluene and xylene may be used, provided that no adverse impact will be inflicted upon the above addition reaction or the like.
  • organic silicon compound represented by the general formula (1) of the invention include those represented by the following structural formulae.
  • Diethynyldiphenylsilane of 34.9 g (0.151 mol), a 0.5 wt% toluene solution of a chloroplatinic acid (H 2 PtCl 6 ⁇ 6H 2 O) of 0.10 g and toluene of 50 mL were put into a 500 mL four-necked separable flask equipped with a mechanical stirrer, a thermometer and a dropping funnel, followed by delivering thereinto 38.5 g (0.315 mol) of trimethoxysilane by drops.
  • H 2 PtCl 6 ⁇ 6H 2 O chloroplatinic acid
  • a composition was obtained in the similar manner as reference example 1, except that 6.6 parts of bis (trimethoxysilyl-ethylene) diphenylsilane was used instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • compositions were obtained in the similar manners as reference examples 1 to 3, except that there were used 4.1 parts of a silicon compound (vinyltrimethoxysilane) represented by the following structural formula (4) instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • compositions were obtained in the similar manners as reference examples 1 to 3, except that there were used 3.8 parts of a silicon compound (methyltrimethoxysilane) represented by the following structural formula (5) instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • a silicon compound methyltrimethoxysilane represented by the following structural formula (5) instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • a composition was obtained in the similar manner as reference example 1, except that there were used 4.5 parts of a silicon compound (1,6-bis (trimethoxysilyl) hexane) represented by the following structural formula (6) instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • a silicon compound (1,6-bis (trimethoxysilyl) hexane) represented by the following structural formula (6) instead of bis (trimethoxysilyl-vinylene) dimethylsilane.
  • each of the compositions obtained in reference examples 1 to 4; and comparative reference examples 1 to 7 was pushed out into a sheet-like shape of a thickness of 2 mm, immediately after they had been produced.
  • the sheet-shaped composition was then exposed to an air of 23 ⁇ 2°C, 50 ⁇ 5% RH, and left under the same atmosphere for three days so as to obtain a cured product whose properties (initial properties) were then measured in accordance with JIS K-6249.
  • a hardness was measured by a hardness meter which was an A-type durometer described in JIS K-6249.
  • Table 1 shows the results of reference examples 1 and 4; and comparative reference examples 1, 4 and 7.
  • Table 2 shows the results of reference example 2; and comparative reference examples 2 and 5.
  • Table 3 shows the results of reference example 3; and comparative reference examples 3 and 6.
  • Measurement result Reference Example 1 Reference Example 4 Comparative Reference Example 1 Comparative Reference Example 4 Comparative Reference Example 7 Tack-free time (min) 5 3 60 ⁇ 60 ⁇ 60 ⁇ Initial RTV 7 days Hardness (Durometer A) 22 25 16 6 24 Elongation (%) 105 130 110 235 0.33
  • the organic silicon compound of the present invention provides a cured product superior in fast curability and durability, and can thus serve as a curing agent component effective for a room temperature-curable organopolysiloxane composition.
  • the present invention is not limited to the above embodiment.
  • the above embodiment is simply an example; and any embodiment belongs to the technical scope of the present invention, if the embodiment has a composition substantially identical to that of the technical ideas described in the claims of the invention, and brings about the similar function effects.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
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EP15782603.3A 2014-04-25 2015-02-02 Verwenduing von bis-(alkoxysilyl-vinylen)-gruppenhaltigen siliziumverbindungen als härter bei raumtemperatur härtbaren organopolysiloxanzusammensetzungen Active EP3135679B1 (de)

Applications Claiming Priority (2)

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JP2014091240 2014-04-25
PCT/JP2015/052809 WO2015162962A1 (ja) 2014-04-25 2015-02-02 新規ビス（アルコキシシリル－ビニレン）基含有ケイ素化合物及びその製造方法

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EP3135679A1 true EP3135679A1 (de) 2017-03-01
EP3135679A4 EP3135679A4 (de) 2017-10-25
EP3135679B1 EP3135679B1 (de) 2019-10-30

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US (2) US20170037066A1 (de)
EP (1) EP3135679B1 (de)
JP (1) JP6187681B2 (de)
KR (1) KR102448206B1 (de)
CN (2) CN109705397B (de)
WO (1) WO2015162962A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4180488A4 (de) * 2020-07-07 2024-08-07 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur schnellhärtende zweikomponentige organopolysiloxanzusammensetzung, gehärtetes produkt daraus und artikel
EP3450480B1 (de) * 2016-04-26 2025-03-26 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur härtbare zusammensetzung enthaltend silanolgruppenterminierte polyoxyalkylenverbindung, dichtungsmaterial und artikel

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Publication number Priority date Publication date Assignee Title
WO2019077942A1 (ja) * 2017-10-17 2019-04-25 信越化学工業株式会社 室温硬化性組成物、シーリング材及び物品
EP3725849B1 (de) 2017-12-15 2022-07-06 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur feuchtigkeitshärtende silikongelzusammensetzung sowie gehärtetes produkt und artikel daraus
JPWO2023068094A1 (de) * 2021-10-19 2023-04-27
JP2024015716A (ja) * 2022-07-25 2024-02-06 信越化学工業株式会社 ビスシラン化合物からなる変性剤、その製造方法及びその使用
JP2024015717A (ja) * 2022-07-25 2024-02-06 信越化学工業株式会社 片末端変性オルガノポリシロキサン及びその製造方法、表面処理剤、並びにシリコーン組成物
CN119954856A (zh) * 2025-02-05 2025-05-09 南开大学 一种烯基多硅氧烷化合物及其制备方法和应用

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3450480B1 (de) * 2016-04-26 2025-03-26 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur härtbare zusammensetzung enthaltend silanolgruppenterminierte polyoxyalkylenverbindung, dichtungsmaterial und artikel
EP4180488A4 (de) * 2020-07-07 2024-08-07 Shin-Etsu Chemical Co., Ltd. Bei raumtemperatur schnellhärtende zweikomponentige organopolysiloxanzusammensetzung, gehärtetes produkt daraus und artikel

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CN109705397B (zh) 2020-11-10
JPWO2015162962A1 (ja) 2017-04-13
KR20160148617A (ko) 2016-12-26
EP3135679B1 (de) 2019-10-30
KR102448206B1 (ko) 2022-09-28
CN109705397A (zh) 2019-05-03
US20170037066A1 (en) 2017-02-09
JP6187681B2 (ja) 2017-08-30
WO2015162962A1 (ja) 2015-10-29
US20180037596A1 (en) 2018-02-08
EP3135679A4 (de) 2017-10-25
CN106255696A (zh) 2016-12-21
US10005799B2 (en) 2018-06-26

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